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The 2018/2019 Offseason: Dates, Deadlines, What and When to Expect Things for the Cubs

The 2018 season did not last nearly as long for the Chicago Cubs as we would have liked, but the brevity of the Cubs’ postseason run – and the method by which they lost the division – only serves to underscore the importance of getting things right this offseason. And with the World Series kicking off tonight, that means the business of the offseason is just around the corner.

But what exactly is “the offseason”? What does it include? What happens when? When do we expect what?

Let’s lay out a road map of the important dates, deadlines, and timelines on the things that will be taking place in the coming months of “the offseason.” Note: we have to use some approximations for dates not yet announced, or dates tied to the undetermined end of the World Series.

October 29 through November 2 – Although players are immediately free agents after the World Series concludes, they cannot sign with a new team for five days. So, while teams can start reaching out to agents, no new contracts can be inked. This five-day period, then, serves as something of an exclusive negotiating window for teams with departing free agents. Usually you don’t see too many deals struck at this time, but it does happen occasionally. Indeed, you sometimes see free agents re-sign with their old team before this window even arrives, as we just saw last night with Eduardo Escobar and the Diamondbacks.)

November 2 – Options are due five days after the World Series. Depending on decisions around baseball, the free agent pool could be further increased. There is also sometimes crazy trade activity in the days leading up to the option decision date (because, for example, Team X might have an option on Player A that they don’t want to pay, but Team Y definitely does want Player A at that option price – so the two teams consummate a trade at the last minute where Team X picks up the option, and then deals Player A to team Y).

The Cubs have several options decisions that will impact their free agents. Pedro Strop will have his $6.25 million option picked up, and Jose Quintana will have his $10.5 million option picked up, without question. Brandon Kintzler will have his $10 million team option declined, but may well pick up his own $5 million player option. The really big question is Cole Hamels’ $20 million team option, for which the $6 million buyout would be paid by the Rangers (but if the Cubs want to exercise the option, they pay the full $20 million).

November 2 – At the end of that five-day window, teams must make decisions on whether make a “qualifying offer” to free agents – in short, in order to receive draft pick compensation should a free agent sign with a new team, his former team must first offer him a one-year deal worth the average of the top 125 salaries in MLB from the previous year. The qualifying offer amount is expected to be around $17.9 million this year. If a player receives a qualifying offer, he can accept it, negotiate a different deal with his former team, or sign with another team, costing that team a pick in the 2018 Draft.

The Cubs will not be extending any qualifying offers this year.

Approximately November 3 to March 2018 – The “Offseason.” The “Hot Stove.” The “Lukewarm Stove.” Whatever you want to call it, this is the meaty period where a team’s roster is built for the subsequent year via free agency, trades, minor league decisions, etc. Generally speaking, the hottest period is from about mid-November until mid-January, but there’s always a ton of stuff that happens outside of that window, too. In fact, in recent years, activity has been pretty hot well into February and March.

November 6 to November 8 – The General Manager Meetings take place in Carlsbad, California. A precursor to the Winter Meetings, the GM Meetings are an initial opportunity for teams to lay some early offseason groundwork for the moves that could come later. Teams also often have organizational meetings around this time.

Approximately November 15 – Players must decide whether to accept the qualifying offer by this date (they used to have just seven days after receiving a QO, but that’s since been increased to ten days). Big-time free agency won’t really get going until after this date, and that’s on the early side.

November 4 to November 15 – The various MLB awards are announced, starting with the Gold Gloves and concluding with the MVPs. The Cubs don’t have a lot of obvious candidates this year, though Javy Baez may at least wind up a finalist for the MVP (Christian Yelich will win). Baez *SHOULD* win a Gold Glove, but you never know.

November 20 – A team’s 40-man roster must be set for the purposes of the Rule 5 Draft (i.e., players already in the organization that the team would like to protect must be added by this date). The Cubs will purge some names from the 40-man roster over the coming weeks, partly to open up spots for Rule 5 purposes. From there, the Cubs will decide on a few young players to add to the 40-man so that they cannot be selected in the Rule 5 Draft (about which, more below).

November 30 – Deadline for tendering contracts to players under team control but not signed for 2018 – i.e., players in their first three years of service time who can be “renewed,” and arbitration-eligible players (players with three or more years of service time, but fewer than six years of service time). This decision will include Kris Bryant, Kyle Hendricks, Javy Baez, Addison Russell, Kyle Schwarber, Mike Montgomery, Carl Edwards Jr., and Tommy La Stella. Note that tendering a contract to these players is optional. Players shy of arbitration level service time are also sometimes non-tendered by this date.

December 10 to December 13 – The Winter Meetings in Las Vegas, Nevada. The gist: MLB executives, agents, and players (as necessary) get together for a week. The Winter Meetings are a notable source of rumors, signings, trades, etc. While not all of the big offseason moves go down at the Meetings, there’s always a ton to discuss (not only amongst ourselves, but also amongst those MLB executives, agents, and players). Last year was especially nuts, with Giancarlo Stanton being traded, Shohei Ohtani choosing the Angels, the Cubs signing Brandon Morrow,

In short, it’s an exciting time for folks who love rumors – like a mini version of the Trade Deadline, but spread out over four days. It’s not quite a Blogathon around here, but it’s pretty close, and we do find ourselves waking up at 3am to quickly check in and make sure nothing is breaking.

December 15 – The Rule Five Draft. The gist: players who’ve been in an organization’s system for a while (several years) without yet reaching the 40-man roster are eligible to be selected by other teams for a small fee, placed on that team’s 25-man roster, and then kept for good if the player can stick on the 25-man roster for almost all of the subsequent season. In recent years, the Cubs have been in much more of a “losing players” mode than “selecting players.”

Approximately December 15 to January 31, 2018 – This is about the time that the Cubs will be sending out non-roster invitations to 2018 Spring Training. The invitations go to prospects and players in the Cubs’ system who’ve not yet been placed on the 40-man roster, as well as veterans who are looking for a 2018 job, but have to “prove it.” You will roll your eyes at most of the minor league free agent non-roster invitees, but it doesn’t hurt to grab as many of the best as possible – and sometimes it pays off.

January 11, 2018 – This is when teams and arbitration-eligible players will submit arbitration requests (each side picks a number – we’ll have more on those details when the dates approach), and then hearings will be set, if necessary, for early February.

January 18 to January 20, 2018 – The Cubs Convention. Fans will get a chance to see, meet, and hear from Cubs players, coaches and management, and the Cubs frequently like to use the Convention as an opportunity to introduce a big offseason acquisition to the fans. You can keep tabs on passes here. It figures to be a fun and busy event, as always.

Approximately February 15, 2018 – Pitchers and catchers report to Spring Training, and your heart climbs up into your throat once again, not to depart for (hopefully) another eight and a half months.

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